Norelgestromin/ethinylestradiol

Norelgestromin/ethinylestradiol

Combination of
Norelgestromin	Progestogen
Ethinylestradiol	Estrogen
Clinical data
Trade names	Ortho Evra, Xulane, Evra, others
AHFS/Drugs.com	Professional Drug Facts
MedlinePlus	a602006
License data	EU EMA: by INN US DailyMed: Norelgestromin_and_ethinyl_estradiol
Pregnancy category	Contraindicated
Routes of administration	Transdermal (patch)
ATC code	G03AA13 (WHO)
Legal status
Legal status	CA: ℞-only[1] UK: POM (Prescription only)[2] US: ℞-only[3][4][5] In general: ℞ (Prescription only)
Identifiers
CAS Number	53016-31-2^Y 57-63-6^Y
PubChem CID	91758695
DrugBank	DB06713 DB00977
ChemSpider	None
UNII	R0TAY3X631 423D2T571U^Y
KEGG	D10839^Y
Chemical and physical data
Formula	C41H53NO4
Molar mass	623.878 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CCC12CCC3C(C1CCC2(C#C)O)CCC4=CC(=NO)CCC34.CC12CCC3C(C1CCC2(C#C)O)CCC4=C3C=CC(=C4)O
InChI InChI=1S/C21H29NO2.C20H24O2/c1-3-20-11-9-17-16-8-6-15(22-24)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2;1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h2,13,16-19,23-24H,3,5-12H2,1H3;1,5,7,12,16-18,21-22H,4,6,8-11H2,2H3/b22-15-;/t16-,17+,18+,19-,20-,21-;16-,17-,18+,19+,20+/m01/s1 Key:KBFRRZPPJPKFHQ-WKXKRCMPSA-N

Norelgestromin/ethinylestradiol, sold under the brand name Ortho Evra among others, is a contraceptive patch containing the progestin norelgestromin and the estrogen ethinylestradiol.[4][6][7]

The most common side effects include headache, nausea (feeling sick), breast tenderness, and irregular uterine bleeding.[6][4]

Norelgestromin/ethinylestradiol is a transdermal patch (a patch that delivers a medicine across the skin).[6] For the first three weeks of the menstrual cycle a new patch should be applied every week, followed by a fourth week, which is patch-free.[6] The patch-free interval must not be longer than seven days; otherwise, additional non-hormonal contraceptive methods must be used, such as condoms.[6] Transdermal patches must always be applied on the same day of the week to the buttock, abdomen (belly), upper arm or upper back.[6] The same area of skin should not be used for two consecutive patches.[6] Norelgestromin/ethinylestradiol may work less well in women weighing 198 pounds (90 kg) or more.[6]

Norelgestromin/ethinylestradiol was approved for medical use in the United States in November 2001, and in the European Union in August 2002.[8][6] It is available as a generic medication.[4][9]

Medical uses

In the United States norelgestromin/ethinylestradiol is indicated for the prevention of pregnancy in women with a BMI < 30 kg/m^2 for whom a transdermal delivery system is an appropriate method of contraception.[4]

In the European Union, norelgestromin/ethinylestradiol is indicated for use as female contraception.[6]

See also

• Combined injectable contraceptive
• Contraceptive vaginal ring
• Oral contraceptive formulations
• List of combined sex-hormonal preparations

References

1. "Evra Product information". Health Canada. 21 June 2018. Retrieved 17 February 2020.
2. "Evra transdermal patch - Summary of Product Characteristics (SmPC)". (emc). 26 June 2020. Archived from the original on 24 October 2020. Retrieved 4 July 2020.
3. "Ortho Evra (norelgestromin/ethinyl estradiol transdermal system) Initial U.S. Approval: 2001". DailyMed. 12 July 2018. Retrieved 4 July 2020.
4. "Xulane- norelgestromin and ethinyl estradiol patch". DailyMed. 7 April 2020. Retrieved 4 July 2020.
5. "Ortho Evra: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 4 July 2020.
6. "Evra EPAR". European Medicines Agency (EMA). 5 August 2008. Retrieved 4 July 2020. Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
7. Graziottin A (2006). "A review of transdermal hormonal contraception : focus on the ethinylestradiol/norelgestromin contraceptive patch". Treatments in Endocrinology. 5 (6): 359–65. doi:10.2165/00024677-200605060-00004. PMID 17107221. S2CID 21033630.
8. "Drug Approval Package: Ortho EVRA (Norelgestromin/Ethinyl Estradiol Transdermal System NDA #21-180". U.S. Food and Drug Administration (FDA). Retrieved 4 July 2020.
9. "Xulane (Norelgestromin and Ethinyl Estradiol Transdermal System), 150 mcg/35 mcg per day" (PDF). Abbreviated New Drug Application. U.S. Food and Drug Administration. 16 April 2014.